Lindsey Buckheit, Kevin Black·May 12, 2025

How 1 Couple Bought 2 Businesses | Lindsey Buckheit & Kevin Black Interview

Lindsey Buckheit and Kevin Black are a married couple who each independently acquired a small business in 2024, having come from corporate careers — Lindsey in product management and operations, Kevin in sales. After eight frustrating months of self-directed searching, they engaged Aquamatch (a buyer-side search firm) and quickly identified two deals: Kevin took over Holdsworth and Nicholas Inc., a 15-year-old media buying ad agency in San Antonio (SDE $575k, purchased for $1.6m at ~2.8x), and Lindsey acquired Collective Creative Outdoors, a residential outdoor design and build company in Austin (SDE $340k, purchased for $1.225m). Both deals were creatively structured with SBA loans and forgivable seller notes tied to gross profit performance to protect against keyman risk and client concentration — the couple even raised the purchase prices above asking in order to induce larger seller notes. The agency deal took six or seven lender conversations before finding a willing SBA lender. The core insight of the episode is the discipline of deal box calibration and how working with a buyer-side firm broke their search logjam; a secondary theme is how two people with distinct skills can acquire different businesses simultaneously, using the stable cash-flowing agency to fund growth ambitions in the design and build.

Deal facts

purchase price: Business 1 (agency): $1.6m; Business 2 (design & build): $1.225m
multiple: Business 1: ~2.8x SDE; Business 2: implied ~3.6x SDE
sde ebitda: Business 1: SDE $575k; Business 2: SDE $340k
revenue: Business 1: $1.2m (2023); Business 2: $750k (2023, down from $1m+ in prior years)
financing structure: Business 1: SBA loan + 36% seller note (5% equity injection carried by seller + 31% forgivable performance note split over year 1 and year 2); buyers brought ~$80k equity. Business 2: SBA loan + 18% seller note (~$225k performance-based note)
notes: Business 1 is Holdsworth and Nicholas Inc., a media buying ad agency in San Antonio, TX. Closed October 4. Business 2 is Collective Creative Outdoors, a residential outdoor design and build company in Austin, TX. Both deals structured with seller-financed forgivable notes tied to gross profit performance to mitigate client concentration and keyman risk. Purchase prices were increased above asking to incentivize sellers to carry larger notes.

Why this business

For the agency: strong and healthy cash flow (SDE $575k well above their $350k threshold), a small existing team staying on, no creative component making it approachable, potential to be fully remote, and Kevin's background in sales and marketing software aligned well. For the design and build: it was in Austin (home market), the seller's biggest challenges (inability to delegate and procrastination) were exactly Lindsay's strengths from years in operations and product management, she was excited to build something tangible, and there was a clear growth path since the seller had done no marketing and the couple now had an ad agency to support it.

What's working

Successful relationship transfer on the agency: three new clients brought on within six months and existing client relationships holding
Forgivable seller note structure provided meaningful downside protection against client concentration and keyman risk on the agency
Seller of design and build business stayed on for six months, actively helping with transition including sharing designer resumes and introductions to contractors
Complementary skill sets between Kevin (sales, account management) and Lindsay (operations, product management) mapped well to the two businesses
Lindsay's father, a general contractor, is moving to the area and can provide expertise and support for the design and build
The ad agency provides cash flow stability while the design and build serves as a growth vehicle
Flat-fee deal team (attorney Barlo and Williams, CPA Midwest CPA) kept process efficient and aligned incentives toward closing

What's hard

Eight months of self-directed search with no deal closed; struggled with too-broad a deal box and scarcity mindset leading to chasing poor-fit deals
Went through six or seven lenders before securing SBA financing for the agency; keyman risk, client concentration, and being a relationship-based business made many banks decline
First QoE provider was hourly and came in significantly over the initial estimate, costing 3-4 weeks of delay
Lindsay is not the subject matter expert in design or architecture and is dependent on the seller's knowledge transfer for the design and build business
The design and build was essentially a one-man shop with all expertise concentrated in the seller
Balancing two businesses simultaneously while Lindsay was still part-time on her old W2 job until her last week before the interview

Notable quotes

I kept finding myself trying to see myself in the business rather than like, does the business work for me. I'm a problem solver. I was always going to try to find a way to make it work.

If you're too broad with your dealbox, there's just too much noise in the businesses that you're looking for. And so, you can never make a decision.

We increased the purchase price to get the seller to take on a note, a performance-based note. So, the purchase price was 1.225. Seller financed about 18% which was the 225. So I increased it by exactly the amount that I wanted seller financed.

On some level, we're betting on ourselves. And that really is what we're doing when we decided to make this change out of the gate is that we were betting on ourselves to be able to come in and do something that we've never done before and to do it well and to make it work.